Classifications

• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
  • A61Q5/00—Preparations for care of the hair
  • A61Q5/06—Preparations for styling the hair, e.g. by temporary shaping or colouring
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K8/00—Cosmetics or similar toiletry preparations
  • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
  • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
  • A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
  • A61K8/87—Polyurethanes
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K8/00—Cosmetics or similar toiletry preparations
  • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
  • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
  • A61K8/73—Polysaccharides
  • A61K8/737—Galactomannans, e.g. guar; Derivatives thereof
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K8/00—Cosmetics or similar toiletry preparations
  • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
  • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
  • A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
  • A61K8/817—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen; Compositions or derivatives of such polymers, e.g. vinylimidazol, vinylcaprolactame, allylamines (Polyquaternium 6)
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K8/00—Cosmetics or similar toiletry preparations
  • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
  • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
  • A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
  • A61K8/817—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen; Compositions or derivatives of such polymers, e.g. vinylimidazol, vinylcaprolactame, allylamines (Polyquaternium 6)
  • A61K8/8182—Copolymers of vinyl-pyrrolidones. Compositions of derivatives of such polymers
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
  • A61Q5/00—Preparations for care of the hair
  • A61Q5/02—Preparations for cleaning the hair
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
  • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
  • A61K2800/54—Polymers characterized by specific structures/properties
  • A61K2800/542—Polymers characterized by specific structures/properties characterized by the charge
  • A61K2800/5424—Polymers characterized by specific structures/properties characterized by the charge anionic
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
  • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
  • A61K2800/54—Polymers characterized by specific structures/properties
  • A61K2800/542—Polymers characterized by specific structures/properties characterized by the charge
  • A61K2800/5426—Polymers characterized by specific structures/properties characterized by the charge cationic

Definitions

• the present invention relates to novel cosmetic compositions with improved properties, intended simultaneously for cleansing, conditioning and styling keratin substances such as the hair, and comprising, in a cosmetically acceptable support, a washing base consisting of surfactants with detergent power, in which are also present cationic polymers in combination with a water-soluble anionic polyurea or a polyurethane.
• the invention also relates to the use of the compositions in the abovementioned cosmetic application.
• detergent hair compositions or shampoos
• conventional surfactants of anionic, nonionic and/or amphoteric type in particular, more particularly of anionic type, for cleansing and/or washing the hair.
• these base compositions have good washing power, but the intrinsic cosmetic properties associated therewith are, nevertheless, fairly poor.
• the relatively aggressive nature of such a cleansing treatment can lead in the long run to more or less pronounced damage to hair fibers, associated in particular with the gradual removal of the lipids or proteins contained in or at the surface of these fibers.
• the conditioners most commonly used to date in shampoos are cationic polymers, which give washed, dry or wet hair an ease of disentangling, a softness and a smoothness that are markedly improved when compared with that which might be obtained with the corresponding cleansing compositions which are free of these polymers.
• washing shampoos which are capable of giving washed hair not only the cosmetic properties mentioned above but also, to a more or less pronounced extent, the properties of styling, volume, shaping and hold.
• These washing shampoos with improved general cosmetic properties are often referred to for simplicity as “styling shampoos”, and this expression will be adopted in the description hereinbelow.
• an anionic polycondensate comprising at least one polyurethane and/or polyurea sequence as defined below, into detergent compositions, in particular hair compositions, containing cationic polymers, it is possible to substantially and significantly improve the cosmetic properties associated with these compositions, while at the same time retaining their good intrinsic washing power.
• polyurethane will be used as being equivalent to a polycondensate comprising at least one polyurethane and/or polyurea sequence.
• novel detergent compositions in particular hair compositions, are now proposed, comprising, in a cosmetically acceptable medium, a washing base, at least one cationic polymer and at least one anionic polycondensate comprising at least one water-soluble polyurethane and/or polyurea sequence.
• a subject of the invention is also the cosmetic use of the above compositions for cleansing, conditioning and styling keratin substances, in particular the hair.
• constituents forming part of the composition of the hair products of the invention are (i) at least one surfactant with detergent power intended to form the washing base, (ii) at least one cationic polymer and (iii) at least one water-soluble anionic polyurethane.
• compositions in accordance with the invention necessarily comprise a washing base, which is generally aqueous.
• the surfactant(s) forming the washing base can either be chosen, alone or as mixtures, from anionic, amphoteric, nonionic, zwitterionic and cationic surfactants.
• the washing base preferably comprises anionic surfactants or mixtures of anionic surfactants and amphoteric surfactants or nonionic surfactants.
• washing base is that amount which is just sufficient to give the final composition a satisfactory foaming and/or detergent power, and excessive amounts of washing base do not really afford any additional advantages.
• the washing base is present in an amount ranging from 4% to 50% by weight, preferably from 6% to 25% by weight, and even more preferably from 8% to 20% by weight, relative to the total weight of the final composition.
• surfactants which are suitable for carrying out the present invention are, in particular, the following:
• anionic surfactants which can be used, alone or as mixtures, in the context of the present invention, mention may be made in particular (non-limiting list) of salts (in particular alkaline salts, especially sodium salts, ammonium salts, amine salts, amino alcohol salts or magnesium salts) of the following compounds: alkyl sulphates, alkyl ether sulphates, alkylamidoether sulphates, alkylarylpolyether sulphates, monoglyceride sulphates; alkyl sulphonates, alkyl phosphates, alkylamide sulphonates, alkylaryl sulphonates, a-olefin sulphonates, paraffin sulphonates; (C 6 -C 24 )alkyl sulphosuccinates, (C 6 -C 24 )alkyl ether sulphosuccinates, (C 6 -C 24 )alkylamide sulphosuccinate
• (C 6 -C 24 )-alkyl polyglycoside carboxylic esters such as alkylglucoside citrates, alkylpolyglycoside tartrates and alkylpolyglycoside sulphosuccinates; alkylsulphosuccinamates; acyl isethionates and N-acyltaurates, the alkyl or acyl radical of all of these various compounds preferably containing from 12 to 20 carbon atoms, and the aryl radical preferably denoting a phenyl or benzyl group.
• anionic surfactants which can also be used, mention may also be made of fatty acid salts such as the salts of oleic, ricinoleic, palmitic and stearic acids, coconut oil acid or hydrogenated coconut oil acid; and acyl lactylates in which the acyl radical contains 8 to 20 carbon atoms.
• alkyl-D-galactosiduronic acids and their salts polyoxy-alkylenated (C 6 -C 24 )alkyl ether carboxylic acids, polyoxyalkylenated (C 6 -C 24 )alkylaryl ether carboxylic acids, polyoxyalkylenated (C 6 -C 24 )alkylamido ether carboxylic acids and their salts, in particular those containing from 2 to 50 alkylene oxide groups in particular ethylene groups, and mixtures thereof.
• Anionic surfactants comprising a carboxylic group are particularly preferred.
• nonionic surfactants are, themselves also, compounds that are well known per se (see in particular in this respect “Handbook of Surfactants” by M. R. Porter, published by Blackie & Son (Glasgow and London), 1991, pp. 116-178), the disclosure of which is hereby incorporated by reference, and, in the context of the present invention, their individual nature is not a critical feature.
• polyethoxylated, polypropoxylated or polyglycerolated fatty acids alkylphenols, a-diols or alcohols having a fatty chain containing, for example, 8 to 18 carbon atoms, it being possible for the number of ethylene oxide or propylene oxide groups to range in particular from 2 to 50 and for the number of glycerol groups to range in particular from 2 to 30.
• copolymers of ethylene oxide and of propylene oxide, condensates of ethylene oxide and of propylene oxide with fatty alcohols polyethoxylated fatty amides preferably having from 2 to 30 mol of ethylene oxide, polyglycerolated fatty amides containing on average 1 to 5, and in particular 1.5 to 4, glycerol groups; polyethoxylated fatty amines preferably having 2 to 30 mol of ethylene oxide; oxyethylenated fatty acid esters of sorbitan having from 2 to 30 mol of ethylene oxide; and fatty acid esters of sucrose, fatty acid esters of polyethylene glycol, alkylpolyglycosides, N-alkylglucamine derivatives, amine oxides such as (C 10 -C 14 )alkylamine oxides or N-acylaminopropylmorpholine oxides.
• the alkylpolyglycosides constitute nonionic surfactants
• amphoteric or zwitterionic surfactants can be, in particular (non-limiting list), aliphatic secondary or tertiary amine derivatives in which the aliphatic radical is a linear or branched chain containing 8 to 18 carbon atoms and containing at least one water-soluble anionic group (for example, carboxylate, sulphonate, sulphate, phosphate or phosphonate); mention may also be made of (C 8 -C 20 )alkylbetaines, sulphobetaines, (C 8 -C 20 )alkylamido(C 1 -C 6 )alkylbetaines and (C 8 -C 20 )alkylamido(C 1 -C 6 )alkylsulphobetaines.
• aliphatic secondary or tertiary amine derivatives in which the aliphatic radical is a linear or branched chain containing 8 to 18 carbon atoms and containing at least one water-soluble anionic group
• R 2 is chosen from an alkyl radical of an acid R 9 —COOH present in hydrolysed coconut oil, a heptyl, nonyl and undecyl radical,
• R 9 is a saturated or unsaturated, linear or branched (C 5 -C 9 ) alkyl
• R′ 3 is a b-hydroxyethyl group
• R 4 is a carboxymethyl group
• B′ is —CH 2 CH 2 OX′
• X′ is chosen from a —CH 2 CH 2 —COOH group and a hydrogen atom
• Y′ is chosen from a —COOH or the —CH 2 —CHOH—SO 3 H radical
• R 2′ is an alkyl radical of an acid R 9 —COOH present in coconut oil or in hydrolysed linseed oil, an alkyl radical, in particular a C 7 , C 9 , C 11 or C 13 alkyl radical, a C 17 alkyl radical and its iso form and an unsaturated C 17 radical.
• R 9 is a saturated or unsaturated, linear or branched (C 5 -C 9 ) alkyl
• cocoamphodiacetate sold under the trade name MIRANOL® C2M concentrate by the company Rhodia Chimie.
• mixtures of surfactants are preferably used, and in particular mixtures of anionic surfactants and mixtures of amphoteric or nonionic surfactants.
• a particularly preferred mixture is a mixture comprising at least one carboxylic anionic surfactant and at least one amphoteric or nonionic surfactant.
• the anionic surfactant preferably used is chosen from polyoxyalkylenated (C 6 -C 24 )alkyl ether carboxylic acids, polyoxyalkylenated (C 6 -C 24 )alkylaryl ether carboxylic acids, polyoxyalkylenated (C 6 -C 24 )-alkylamido ether carboxylic acids and a mixture thereof with a sulphonated or sulphated surfactant such as sodium, triethanolamine or ammonium (C 12 -C 14 )alkyl sulphates, sodium (C 12 -C 14 )alkyl ether sulphates oxyethylenated with 2.2 mol of ethylene oxide, sodium cocoyl isethionate and mixtures thereof with:
• an amphoteric surfactant such as the amine derivatives known as disodium cocoamphodipropionate or sodium cocoamphopropionate, sold in particular by the company Rhodia Chimie under the trade name MIRANOL® C2M CONC. as an aqueous solution containing 38% active material, or under the name MIRANOL® C32;
• alkylbetaines in particular the cocoylbetaine sold under the name DEHYTON® AB 30 as an aqueous solution containing 32% AM by the company Henkel or alkylamidoalkylbetaines such as TEGOBETAINE® F50 sold by the company Goldschmidt,
• cationic surfactants mention may be made in particular (non-limiting list) of: salts of primary, secondary or tertiary fatty amines, which are if optionally polyoxyalkylenated; quaternary ammonium salts such as tetraalkylammonium, alkylamidoalkyl-trialkylammonium, trialkylbenzylammonium, trialkyl-hydroxyalkylammonium or alkylpyridinium chlorides or bromides; imidazoline derivatives; and amine oxides of cationic nature.
• salts of primary, secondary or tertiary fatty amines which are if optionally polyoxyalkylenated
• quaternary ammonium salts such as tetraalkylammonium, alkylamidoalkyl-trialkylammonium, trialkylbenzylammonium, trialkyl-hydroxyalkylammonium or alkylpyridinium chlorides or bromides
• cationic surfactants whose use is not excluded, do not constitute preferred surfactants for carrying out the present invention.
• compositions in accordance with the invention also comprise a cationic polymer.
• the conditioners of cationic polymer type which can be used in accordance with the present invention can be chosen from any of those already known per se as enhancing the cosmetic properties of hair treated with detergent compositions, namely, in particular, those described in patent application EP-A-0,337,354 and in French patent applications FR-A-2,270,846, 2,383,660, 2,598,611, 2,470,596 and 2,519,863, the disclosures of all of which are hereby incorporated by reference.
• cationic polymer denotes any polymer containing cationic groups and/or groups which can be ionized into cationic groups.
• the preferred cationic polymers are chosen from those which contain units containing primary, secondary, tertiary and/or quaternary amine groups which can either form part of the main polymer chain or which can be carried by a lateral substituent that is directly attached thereto.
• the cationic polymers generally used have a number-average molecular mass of from 500 to 5 ⁇ 10 6 approximately, and preferably from 1000 to 3 ⁇ 10 6 approximately.
• cationic polymers mention may be made more particularly of polymers of polyquaternary ammonium, polyamino amide and polyamine type. These are known products.
• polymers of the polyquaternary ammonium, polyamino amide and polyamine type which can be used in accordance with the present invention and which may be mentioned in particular, are those described in French Patent Nos. 2,505,348 or 2,542,997, the disclosures of both of which are hereby incorporated by reference. Among these polymers, mention may be made of the polymers set forth below.
• R 3 which may be identical or different, is chosen from a hydrogen atom and a CH 3 radical;
• A which may be identical or different, is chosen from a linear or branched alkyl group of 1 to 6 carbon atoms, preferably 2 or 3 carbon atoms, and a hydroxyalkyl group of 1 to 4 carbon atoms;
• R 4 , R 5 and R 6 which may be identical or different, are chosen from an alkyl group containing from 1 to 18 carbon atoms or a benzyl radical and preferably an alkyl group containing from 1 to 6 carbon atoms;
• R 1 and R 2 which may be identical or different, are chosen from hydrogen and an alkyl group containing from 1 to 6 carbon atoms and preferably methyl or ethyl;
• X is an anion derived from an inorganic or organic acid such as a methosulphate anion or halide such as chloride or bromide.
• the copolymers of the family (1) can also contain one or more units derived from comonomers which can be chosen from the family of acrylamides, methacrylamides, diacetone acrylamides, acrylamides and methacrylamides substituted on the nitrogen with lower alkyls (C 1 -C 4 ), acrylic or methacrylic acids or esters thereof, vinyllactams such as vinylpyrrolidone or vinylcaprolactam, and vinyl esters.
• comonomers which can be chosen from the family of acrylamides, methacrylamides, diacetone acrylamides, acrylamides and methacrylamides substituted on the nitrogen with lower alkyls (C 1 -C 4 ), acrylic or methacrylic acids or esters thereof, vinyllactams such as vinylpyrrolidone or vinylcaprolactam, and vinyl esters.
• copolymers of acrylamide and of dimethylaminoethyl methacrylate quaternized with dimethyl sulphate or with a dimethyl halide such as that sold under the name HERCOFLOC by the company Hercules,
• copolymers of acrylamide and of methacryloyloxyethyltrimethylammonium chloride described, for example, in patent application EP-A-080976, the disclosure of which is hereby incorporated by reference, and sold under the name BINA QUAT P 100 by the company Ciba Geigy,
• quaternized or non-quaternized vinylpyrrolidone/ dialkylaminoalkyl acrylate or methacrylate copolymers such as the products sold under the name GAFQUAT by the company ISP such as, for example, GAFQUAT 734 or GAFQUAT 755 or the products known as COPOLYMER 845, 958 and 937.
• dimethylaminoethyl methacrylate/vinylcaprolactam/ vinylpyrrolidone terpolymers such as the product sold under the name GAFFIX VC 713 by the company ISP,
• Cationic cellulose derivatives such as cellulose copolymers or cellulose derivatives grafted with a water-soluble monomer of quaternary ammonium, and described in particular in U.S. Pat. No. 4,131,576, the disclosure of which is hereby incorporated by reference, such as hydroxyalkylcelluloses, for instance hydroxymethyl-, hydroxyethyl- or hydroxypropylcelluloses grafted, in particular, with a methacryloylethyltrimethylammonium, methacrylamidopropyltrimethylammonium or dimethyldiallylammonium salt.
• hydroxyalkylcelluloses for instance hydroxymethyl-, hydroxyethyl- or hydroxypropylcelluloses grafted, in particular, with a methacryloylethyltrimethylammonium, methacrylamidopropyltrimethylammonium or dimethyldiallylammonium salt.
• the commercial products corresponding to these cationic cellulose derivatives are more particularly the products sold under the names CELQUAT L 200 and CELQUAT H 100 by the company National Starch.
• cationic polysaccharides described more particularly in U.S. Pat. Nos. 3,589,578 and 4,031,307, the disclosures of both of which are hereby incorporated by reference, such as guar gums containing cationic trialkylammonium groups. Guar gums modified with a salt (e.g., chloride) of 2,3-epoxypropyltrimethylammonium are used, for example.
• a salt e.g., chloride
• Such products are sold in particular under the trade names JAGUAR C13 S, JAGUAR C 15, JAGUAR C 17 or JAGUAR C162 by the company Meyhall.
• Water-soluble polyamino amides prepared in particular by polycondensation of an acidic compound with a polyamine. These polyamino amides can be crosslinked with an epihalohydrin, a diepoxide, a dianhydride, an unsaturated dianhydride, a bis-unsaturated derivative, a bis-halohydrin, a bis-azetidinium, a bis-haloacyldiamine, a bis-alkyl halide or alternatively with an oligomer resulting from the reaction of a difunctional compound which is reactive with a bis-halohydrin, a bis-azetidinium, a bis-haloacyldiamine, a bis-alkyl halide, an epihalohydrin, a diepoxide or a bis-unsaturated derivative.
• the crosslinking agent is used in proportions ranging from 0.025 to 0.35 mol per amine group of the polyamino amide.
• These polyamino amides can be alkylated or, if they contain one or more tertiary amine functions, they can be quaternized.
• Such polymers are described, in particular, in French Patent Nos. 2,252,840 and 2,368,508, the disclosures of which are hereby incorporated by reference.
• polyamino amide derivatives resulting from the condensation of polyalkylene polyamines with polycarboxylic acids followed by alkylation with difunctional agents Mention may be made, for example, of adipic acid/dialkylaminohydroxyalkyldialkylenetriamine polymers in which the alkyl radical contains from 1 to 4 carbon atoms and preferably denotes methyl, ethyl or propyl.
• alkyl radical contains from 1 to 4 carbon atoms and preferably denotes methyl, ethyl or propyl.
• Such polymers are described in particular in French patent 1,583,363, the disclosure of which is hereby incorporated by reference.
• adipic acid/dimethylaminohydroxypropyl/diethylenetriamine polymers sold under the name CARTARETINE F, F4 or F8 by the company Sandoz.
• the molar ratio between the polyalkylene polyamine and the dicarboxylic acid is from 0.8:1 to 1.4:1.
• the polyamino amide resulting therefrom is reacted with epichlorohydrin in a molar ratio of epichlorohydrin relative to the secondary amine group of the polyamino amide of from 0.5:1 to 1.8:1.
• Such polymers are described in particular in U.S. Pat. Nos. 3,227,615 and 2,961,347, the disclosures of which are hereby incorporated by reference.
• Polymers of this type are sold in particular under the name HERCOSETT 57 by the company Hercules Inc. or alternatively under the name PD 170 or DELSETTE 101 by the company Hercules in the case of the adipic acid/epoxypropyl/diethylenetriamine copolymer.
• k and t are equal to 0 or 1, the sum k+t being equal to 1;
• R 12 is chosen from a hydrogen atom and a methyl radical
• R 10 and R 11 which may be the same or different, are chosen from an alkyl group having from 1 to 22 carbon atoms, a hydroxyalkyl group in which the alkyl group preferably has 1 to 5 carbon atoms, or a lower amido-(C 1 -C 4 )alkyl group, or R 10 and R 11 can denote, together with the nitrogen atom to which they are attached, heterocyclic groups such as piperidyl or morpholinyl;
• Y ⁇ is an anion such as bromide, chloride, acetate, borate, citrate, tartrate, bisulphate, bisulphite, sulphate or phosphate.
• R 10 and R 11 which may be the same or different, preferably are chosen from an alkyl group containing from 1 to 4 carbon atoms.
• dimethyidiallylammonium chloride homopolymer sold under the name MERQUAT 100 by the company Calgon and its homologues of low weight-average molecular mass and copolymers of diallyldimethylammonium chloride and of acrylamide sold under the name MERQUAT 550.
• R 13 , R 14 , R 15 and R 16 which may be identical or different, are chosen from aliphatic, alicyclic or arylaliphatic radicals containing from 1 to 20 carbon atoms or lower hydroxyalkylaliphatic radicals, or alternatively R 13 , R 14 , R 15 and R 6 , together or separately, constitute, with the nitrogen atoms to which they are attached, heterocycles optionally containing a second heteroatom other than nitrogen, or alternatively R 13 , R 14 , R 15 and R 16 represent a linear or branched C 1 -C 6 alkyl radical substituted with a nitrile, ester, acyl or amide group or a group —CO—O—R 17 —D or —CO—NH—R 17 —D where R 17 is an alkylene and D is a quaternary ammonium group;
• a 1 and B′ 1 which may be identical or different, are chosen from polymethylene groups containing from 2 to 20 carbon atoms which may be linear or branched, saturated or unsaturated, and which may contain, linked to or intercalated in the main chain, one or more aromatic rings or one or more oxygen or sulphur atoms or sulphoxide, sulphone, disulphide, amino, alkylamino, hydroxyl, quaternary ammonium, ureido, amide or ester groups, and
• X ⁇ is an anion derived from an inorganic or organic acid
• a 1 , R 13 and R 15 can form, with the two nitrogen atoms to which they are attached, a piperazine ring; in addition, if A 1 denotes a linear or branched, saturated or unsaturated alkylene or hydroxyalkylene radical, B 1 can also denote a group (CH 2 ) n —CO—D—OC—(CH 2 ) n —
• n is an integer from 1 to 6
• D is chosen from:
• x and y are chosen from an integer from 1 to 4, representing a defined and unique degree of polymerization or any number from 1 to 4 representing an average degree of polymerization;
• a bis-secondary diamine residue such as a piperazine derivative
• X ⁇ is an anion such as chloride or bromide.
• These polymers generally have a number-average molecular mass of from 1000 to 100,000.
• R 1 , R 2 , R 3 and R 4 which may be identical or different, are chosen from an alkyl or hydroxyalkyl radical containing from 1 to 4 carbon atoms approximately,
• n and p are integers ranging from 2 to 20 approximately, and
• X ⁇ is an anion derived from an inorganic or organic acid.
• R 18 , R 19 , R 20 and R 21 which may be identical or different, are chosen from a hydrogen atom or a methyl, ethyl, propyl, b-hydroxyethyl, b-hydroxypropyl and —CH 2 CH 2 (OCH 2 CH 2 ) p OH radical,
• r and s which may be identical or different, are integers from 1 to 6,
• q is equal to 0 or to an integer between 1 and 34
• X is a halogen atom
• A is chosen from a dihalide radical and preferably the radical —CH 2 —CH 2 —O—CH 2 —CH 2 —.
• MIRAPOL A 15 MIRAPOL AD1, MIRAPOL AZ1 and MIRAPOL 175 sold by the company Miranol.
• Quaternary polymers of vinylpyrrolidone and of vinylimidazole such as, for example, the products sold under the names LUVIQUAT FC 905, FC 550 and FC 370 by the company BASF.
• Polyamines such as POLYQUART H sold by Henkel under the reference name “Polyethylene glycol (15) tallow polyamine” in the CTFA dictionary.
• Crosslinked polymers of methacryloyloxy(C 1 -C 4 )alkyltri(C 1 -C 4 )-alkylammonium salts such as the polymers obtained by homopolymerization of dimethylaminoethyl methacrylate quaternized with methyl chloride, or by copolymerization of acrylamide with dimethylaminoethyl methacrylate quaternized with methyl chloride, the homo- or copolymerization being followed by crosslinking with a compound containing olefinic unsaturation, in particular methylenebisacrylamide.
• a crosslinked acrylamide/methacryloyloxyethyltrimethyl-ammonium chloride copolymer (20/80 by weight) in the form of a dispersion containing 50% by weight of the copolymer in mineral oil can be used more particularly.
• This dispersion is sold under the name SALCARE® SC 92 by the company Allied Colloids.
• a crosslinked methacryloyloxyethyltrimethylammonium chloride homopolymer containing about 50% by weight of the homopolymer in mineral oil or in a liquid ester can also be used. These dispersions are sold under the names SALCARE® SC 95 and SALCARE® SC 96 by the company Allied Colloids.
• cationic polymers which can be used in the context of the invention are polyalkyleneimines, in particular polyethyleneimines, polymers containing vinylpyridine or vinylpyridinium units, condensates of polyamines and of epichlorohydrin, quaternary polyureylenes and chitin derivatives.
• quaternary cellulose ether derivatives such as the products sold under the name JR 400 by the company Union Carbide Corporation, cyclopolymers, in particular the polymers or copolymers of dimethyldiallylammonium chloride and of acrylamide, sold under the names MERQUAT 100, MERQUAT 550 and MERQUAT S by the company Calgon, cationic polysaccharides such as the guar gums modified with 2,3-epoxypropyltrimethylammonium chloride sold under the name JAGUAR C13S by the company Meyhall and the vinylpyrrolidone/methacrylamidopropyldimethylamine copolymers sold in particular under the name STYLEZE CC 10 by the company ISP, and mixtures thereof.
• quaternary cellulose ether derivatives such as the products sold under the name JR 400 by the company Union Carbide Corporation, cyclopolymers, in particular the polymers or copolymers of dimethyldiallylammonium chloride and
• the cationic polymer(s) can represent from 0.01% to 10% by weight, preferably from 0.05% to 5% by weight and even more preferably from 0.1% to 3% by weight, relative to the total weight of the final composition.
• the detergent hair compositions in accordance with the invention also contain at least one polycondensate comprising at least one polyurethane and/or polyurea sequence, the polycondensate being water-soluble.
• polycondensates comprising at least one polyurethane and/or polyurea sequence to which the present invention is particularly directed are those described in patents EP 0,751,162, EP 0,637,600, FR 2,743,297 and EP 0,648,485, of which L'Oréal is the proprietor, as well as patents EP 0,656,021 or WO 94/03510 from the company BASF and EP 0,619,111 from the company National Starch, the disclosures of all of which are hereby incorporated by reference.
• the polycondensates used in accordance with the invention are water-soluble, either in the acid form or after partial or total neutralization with an organic or inorganic base.
• the water-soluble polymers according to the present invention are those which give, when dissolved in water, compositions that are clear to the naked eye (at a concentration at least equal to 1% of active material and at room temperature (20-25° C.)).
• the polycondensate can be formed by an arrangement of blocks, this arrangement being obtained in particular from:
• the compounds (1) are chosen from the group comprising diols, diamines, polyesterols, polyetherols or a mixture thereof.
• the compounds (1) which are preferred are linear polyethylene and polypropylene glycols, in particular those obtained by reaction of ethylene oxide or propylene oxide with water or diethylene glycol or dipropylene glycol in the presence of sodium hydroxide as catalyst.
• These polyglycols generally have a molecular weight from about 600 to 20,000.
• polyhydroxy compounds such as polyether diols, polyester diols, polyacetal diols, polyamide diols, polyester polyamide diols, poly(alkylene ether) diols, polythioether diols and polycarbonate diols.
• the preferred polyether diols are, for example, the products of condensation of ethylene oxide, of propylene oxide or of tetrahydrofuran, the grafted or block copolymerization or condensation products thereof, such as mixtures of ethylene ioxide and propylene oxide condensates, and products of polymerization of olefins, under high pressure, with alkylene oxide condensates.
• Suitable polyethers are prepared, for example, by condensation of alkylene oxides and polyhydric alcohols, such as ethylene glycol, 1,2-propylene glycol and 1,4-butanediol.
• polyester diols, polyester amides and polyamide diols are preferably saturated and are obtained, for example, from the reaction of saturated or unsaturated polycarboxylic acids with polyhydric alcohols, diamines or polyamines.
• Adipic acid, succinic acid, phthalic acid, isophthalic acid, terephthalic acid and maleic acid can be used, for example, to prepare these compounds.
• Suitable polyhydric alcohols for preparing the polyesters include, for example, ethylene glycol, diethylene glycol, 1,2-propylene glycol, 1,4-butanediol, neopentyl glycol and hexanediol.
• Amino alcohols, for example ethanolamine can also be used.
• Suitable diamines for preparing the polyester amides are ethylenediamine and hexamethylenediamine.
• Suitable polyacetals can be prepared, for example, from 1,4-butanediol or hexanediol and formaldehyde.
• Suitable polythioethers can be prepared, for example, by condensation reaction between thioglycols either alone or in combination with other glycols such as ethylene glycol, 1,2-propylene glycol or with other polyhydroxylated compounds.
• Polyhydroxylated compounds already containing urea or urethane groups, natural polyols, which can be further modified, for example castor oil and carbohydrates, can also be used.
• the compound of group (1) is a polyesterol, in particular a polyester diol formed by the reaction of at least one (di)polyol (1 a ) and of at least one acid (1 b ).
• the (di)polyol (1 a ) is chosen in particular from the group comprising neopentyl glycol, 1,4-butanediol, hexanediol, ethylene glycol, diethylene glycol, propylene glycol, butylene glycol, neopentyl glycol and (di)polyethylene glycol.
• the acid (1 b ) is chosen in particular from the group comprising phthalic acid, isophthalic acid, adipic acid and (poly)lactic acid.
• the compounds (2) which may be used in particular are a hydroxycarboxylic acid such as dimethylolpropanoic acid (DMPA) or a 2,2-hydroxymethylcarboxylic acid.
• DMPA dimethylolpropanoic acid
• the compound (2) is useful as a coupling block.
• the compounds (2) which are particularly preferred in accordance with the invention are those chosen from the group comprising 2,2-di(hydroxymethyl)-acetic acid, 2,2-dihydroxymethylpropionic acid, 2,2-dihydroxymethylbutyric acid and 2,2-dihydroxymethylpentanoic acid.
• the di- or polyisocyanate (3) can be chosen in particular from the group comprising hexamethylene diisocyanate, isophorone diisocyanate (IPDI), tolylene diisocyanate, diphenylmethane 4,4′-diisocyanate (DPMD) and dicyclohexylmethane 4,4′-diisocyanate (DCMD), methylenebis(p-phenyl) diisocyanate, methylenebis(4-cyclohexyl isocyanate), toluene diisocyanate, 1,5-naphthalene diisocyanate, 4,4′-diphenylmethane diisocyanate, 2,2′-dimethyl-4,4′-diphenyl methane diisocyanate, 1,3-phenylene diisocyanate, 1,4-phenylene diisocyanate, mixtures of 2,4- and 2,6-toluene diisocyanate, 2,2′-dichloro
• the polycondensate can be formed using an additional compound (4) which generally serves to lengthen the polycondensate chain.
• These compounds (4) can be chosen from the group comprising, in particular, saturated or unsaturated glycols such as ethylene glycol, diethylene glycol, neopentyl glycol, triethylene glycol, amino alcohols such as ethanolamine, propanolamine or butanolamine, heterocyclic, aromatic, cycloaliphatic and aliphatic primary amines, diamines, carboxylic acids such as aliphatic, aromatic and heterocyclic carboxylic acids, for instance oxalic acid, succinic acid, glutaric acid, adipic acid, sebacic acid or terephthalic acid, and aminocarboxylic acids.
• the preferred compounds (4) are aliphatic diols.
• polyurethane-1 (INCI name) sold by BASF under the name LUVISET PURE.
• the polycondensates in accordance with the invention can also be formed from additional compounds (5) having a silicone skeleton, such as polysiloxanes, polyalkylsiloxanes or polyarylsiloxanes, in particular polyethylsiloxanes, polymethylsiloxanes and polyphenylsiloxanes, optionally comprising hydrocarbon-based chains grafted onto silicon atoms.
• additional compounds (5) having a silicone skeleton such as polysiloxanes, polyalkylsiloxanes or polyarylsiloxanes, in particular polyethylsiloxanes, polymethylsiloxanes and polyphenylsiloxanes, optionally comprising hydrocarbon-based chains grafted onto silicon atoms.
• polyurethane and/or polyurea sequences of the polymer which are used advantageously contain a base repeating unit corresponding to the general formula below:
• radicals X′ which may be identical or different, are chosen from O and NH,
• B is a divalent hydrocarbon-based radical, this radical being substituted or unsubstituted
• R is a divalent radical chosen from alkylene radicals of aromatic, (C 1 to C 20 ) aliphatic or (C 1 to C 20 ) cycloaliphatic type, these radicals being substituted or unsubstituted.
• the radical B is a (C 1 to C 30 ) radical and bears a group containing one or more carboxylic function(s) and/or one or more sulphonic function(s), the said carboxylic and/or sulphonic functions being in free form or else partially or totally neutralized with an inorganic or organic base.
• radical R is chosen from hexamethylene, 4,4′-biphenylenemethane, 2,4- and/or 2,6-tolylene, 1,5-naphthylene, p-phenylene and methylene4,4-bis(cyclohexyl) radicals and the divalent radical derived from isophorone.
• polycondensate used in accordance with the invention comprising at least one polyurethane and/or polyurea sequence can advantageously also comprise at least one polysiloxane sequence in which the base repeating unit corresponds, for example, to the general formula (II′) below:
• P is a polysiloxane segment
• radicals X′ which may be identical or different, are chosen from O and NH, and
• R is a divalent radical chosen from alkylene radicals of aromatic, C 1 to C 20 aliphatic or C 1 to C 20 cycloaliphatic type, these radicals being substituted or unsubstituted.
• polysiloxane segment P corresponds to the general formula below:
• radicals A which may be identical or different, are chosen, on the one hand, from C 1 to C 20 monovalent hydrocarbon-based radicals which are free or substantially free of ethylenic unsaturation, and, on the other hand, from aromatic radicals,
• Y is a divalent hydrocarbon-based radical
• z is an integer chosen such that the average molecular weight of the polysiloxane segment is from 300 to 10,000.
• the divalent radical Y is chosen from alkylene radicals of formula —(CH 2 ) a —, in which a represents an integer which can be from 1 to 10.
• the radicals A can be chosen from alkyl radicals, in particular methyl, ethyl, propyl, isopropyl, butyl, pentyl, hexyl, octyl, decyl, dodecyl and octadecyl radicals, cycloalkyl radicals, in particular a cyclohexyl radical, aryl radicals, in particular phenyl and naphthyl, arylalkyl radicals, in particular benzyl and phenylethyl, as well as tolyl and xylyl radicals.
• alkyl radicals in particular methyl, ethyl, propyl, isopropyl, butyl, pentyl, hexyl, octyl, decyl, dodecyl and octadecyl radicals
• cycloalkyl radicals in particular a cyclohexyl radical
• the hair compositions in accordance with the invention contain the polyurethanes (polycondensates) defined above in weight contents which can be from 0.05% to 10%, preferably from 0.1% to 5%, relative to the total weight of the composition.
• the cationic polymer/polyurethane ratio is from 0.001:1 to 200:1, preferably from 0.02:1 to 50:1, and even more particularly from 0.1:1 to 20:1.
• the cosmetically acceptable aqueous medium can consist solely of water or of a mixture of water and a cosmetically acceptable solvent such as a (C 1 -C 4 ) lower alcohol, for instance ethanol, isopropanol, tert-butanol or n-butanol; alkylene glycols such as propylene glycol, and glycol ethers.
• a cosmetically acceptable solvent such as a (C 1 -C 4 ) lower alcohol, for instance ethanol, isopropanol, tert-butanol or n-butanol
• alkylene glycols such as propylene glycol, and glycol ethers.
• the detergent compositions according to the invention have a final pH generally of from 3 to 10. Preferably, this pH is from 4 to 9. Adjustment of the pH to the desired value can be carried out conventionally by adding a base (organic or inorganic base) to the composition, for example aqueous ammonia or a primary, secondary or tertiary (poly)amine such as monoethanolamine, diethanolamine, triethanolamine, isopropanolamine or 1,3-propanediamine, or alternatively by adding an inorganic or organic acid, preferably carboxylic acid such as, for example, citric acid.
• a base organic or inorganic base
• a base organic or inorganic base
• a base for example aqueous ammonia or a primary, secondary or tertiary (poly)amine such as monoethanolamine, diethanolamine, triethanolamine, isopropanolamine or 1,3-propanediamine
• an inorganic or organic acid preferably carboxylic acid such as, for example, citric acid
• compositions in accordance with the invention can contain, in addition to the combination defined above, viscosity modifiers such as electrolytes, or thickeners. Mention may be made in particular of sodium chloride, sodium xylenesulphonate, scleroglucanes, xanthan gums, fatty acid alkanolamides, alkyl ether carboxylic acid alkanolamides optionally oxyethylenated with up to 5 mol of ethylene oxide, such as the product sold under the name AMINOL A5 by the company Chem Y, crosslinked polyacrylic acids and crosslinked acrylic acid/(C 10 -C 30 ) alkyl acrylate copolymers. These viscosity regulators are used in the compositions according to the invention in proportions which can range up to 10% by weight relative to the total weight of the composition.
• compositions in accordance with the invention can also contain up to 5% of pearlescent agents or opacifiers that are well known in the state of the art, such as, for example, (C 16 ) higher fatty alcohols, sodium or magnesium palmitate, sodium or magnesium stearate or hydroxystearate, acyl derivatives containing a fatty chain, such as the monostearates or distearates of ethylene glycol or of polyethylene glycol, and ethers containing a fatty chain such as, for example, distearyl ether or 1-(hexadecyloxy)-2-octadecanol.
• pearlescent agents or opacifiers that are well known in the state of the art, such as, for example, (C 16 ) higher fatty alcohols, sodium or magnesium palmitate, sodium or magnesium stearate or hydroxystearate, acyl derivatives containing a fatty chain, such as the monostearates or distearates of ethylene glycol or of polyethylene glycol,
• the detergent compositions according to the invention can also contain any adjuvant commonly encountered in shampoos, such as, for example, fragrances, preserving agents, sequestering agents, thickeners, softeners, foam modifiers, dyes, pearlescent agents, moisturizers, antidandruff agents, anti-seborrhoeic agents, sunscreens and the like.
• adjuvant commonly encountered in shampoos such as, for example, fragrances, preserving agents, sequestering agents, thickeners, softeners, foam modifiers, dyes, pearlescent agents, moisturizers, antidandruff agents, anti-seborrhoeic agents, sunscreens and the like.
• compositions in accordance with the invention can optionally also contain other agents which have an effect of improving the cosmetic properties of the hair or the skin without, however, adversely affecting the stability of the compositions.
• agents which have an effect of improving the cosmetic properties of the hair or the skin without, however, adversely affecting the stability of the compositions.
• compositions according to the invention can also contain foam synergists such as (C 10 -C 18 ) 1,2-alkanediols or fatty alkanolamides derived from mono- or diethanolamine.
• foam synergists such as (C 10 -C 18 ) 1,2-alkanediols or fatty alkanolamides derived from mono- or diethanolamine.
• compositions can be in the form of more or less thickened liquids, creams or gels and they are mainly suitable for washing, caring for and/or styling the hair.
• compositions in accordance with the invention are used as conventional shampoos, they are simply applied to wet hair and the lather generated by massaging or friction with the hands is then removed, after optionally leaving the shampoo on the hair for a period of time, by rinsing with water, it being possible for the operation to be repeated one or more times.
• compositions in accordance with the invention give the hair, after rinsing, a noteworthy styling effect which is manifested in particular by an ease of styling and of hold, as well as providing markedly improved volume and lightness.
• a subject of the invention is also a process for washing and conditioning keratin substances such as the hair, which consists in applying an effective amount of a composition as defined above to the wet substances, followed by rinsing with water after optionally leaving the composition on the hair for a period of time.
• LUVISET PURE (BASF) polyurethane-1 (INCI name) as an aqeuous-alcoholic solution containing 30% active material are water-soluble polyurethane;
• AVALURE UR 450 (Goodrich) propylene glycol/isophorone diisocyanate/ dimethylolpropanoic acid copolymer as an aqueous dispersion containing 38% active material, are water-insoluble polyurethane
• MERQUAT 100 (Calgon) diallyidimethylammonium chloride homopolymer as an aqueous solution containing 40% active material
• MERQUAT 550 (Calgon) diallyldimethylammonium chloride/acrylamide copolymer 50/50 (by weight) as an aqueous solution containing 8% active material.
• JAGUAR C 13 S (Rhodia Chimie) hydroxypropylguar trimethylammonium chloride.
• DEHYTON AB 30 (Henkel) cocoylbetaine as an aqueous solution containing 30% active material.
• composition A Two shampoo compositions were prepared, one in accordance with the invention (composition A) and the other comparative (composition B), differing from each other simply by the nature of the anionic polymer used:
• a panel of 10 testers was presented with the locks prepared as indicated above.
• the 10 judges were unanimous and declared that the hair treated with composition A was softer and smoother.
• fixing properties means the cohesion provided to a body of hair by depositing a material which limits the relative displacement of the hair as well as the stability over time of the body of hair formed.
• the length (L) of the wound locks suspended via their own weight was then measured in front of a graduated panel.
• the locks were then allowed to relax, still in the suspended state, for up to 4 hours at room temperature.
• the length of the suspended locks then increased by a certain length (DL).
• DL certain length
• a (invention) B LT0 12.6 10.8 12 13.5 LT2 15 13.5 15 16.5 LT4 15.5 14 15.5 17 % elongation at 2 H 19.0 25.0 25.0 22.2 average of 2 H 22 23.6 % elongation at 4 H 23.0 29.6 29.1 25.9 average of 4 H 26.3 27.5
• composition B With composition B, the elongation at 2 hours was 3 cm (average for 2 locks), whereas it was only 2.55 cm (average for 2 locks) for composition A, i.e., an improvement in the reduction of the elongation by more than 15%. At four hours, the elongation with composition B was 4.01 cm (average for 2 locks), while it was only 3.05 cm (average for 2 locks) for composition A. Thus, these results clearly reflects the better holding of the hairstyle obtained by means of the shampoo according to the invention.
• composition A Two shampoo compositions were prepared, one in accordance with the invention (composition A) and the other comparative (composition C), differing from each other simply by the solubility of the anionic polyurethane used:
• AVALURE UR 450 is a water-insoluble anionic polyurethane.
• a panel of 10 testers was presented with the locks prepared as indicated above.
• the 10 judges were unanimous and declare that the hair treated with composition A was softer and smoother.
• the length of the suspended locks then increased by a certain length (DL).
• a (invention) B LT0 12.6 10.8 11.8 12.0 LT2 15 13.5 15.5 15.5 LT4 15.5 14 16 16 % elongation at 2 H 19.0 25.0 31.3 29.2 average of 2 H 22 30.2 % elongation at 4 H 23.0 29.6 35.6 33.3 average of 4 H 26.3 34.4
• composition C With composition C, the elongation at 2 hours was 3.6 cm (average for 2 locks), whereas it was only 2.55 cm (average for 2 locks) for composition A, i.e., an improvement in the reduction of the elongation by more than 29%. At four hours, the elongation with composition C was 4.1 cm (average for 2 locks), while it was only 3.05 cm (average for 2 locks) for composition A. Thus, these results clearly which clearly reflects the better hold of the hairstyle obtained by means of the shampoo according to the invention.
• a shampoo in accordance with the invention having the composition below was prepared:
• a shampoo in accordance with the invention having the composition below was prepared:
• sodium lauryl ether sulphate (2.2 EO) 15.5 g AM cocoylbetaine (DEHYTON AB 30 from Henkel) 2.4 g AM JAGUAR C 13 S (Rhodia) 0.05 g AM LUVISET PURE (BASF) 1 g AM polydimethylsiloxane 2.7 g AM 1-(hexadecyloxy)-2-octadecanol/ 2.5 g AM cetyl alcohol coconut acid monoisopropanolamide 1 g AM sodium cetostearyl sulphate 0.75 g AM preserving agent qs water qs 100 g pH adjusted to 7
• a shampoo in accordance with the invention having the composition below was prepared:
• BEAUFLIGHT SHAA (Sanyo Kasei) 3 g AM AG 10 LK (KAO) 12 g AM MERQUAT 100 from Calgon 1 g AM LUVISET PURE (BASF) 3 g AM sodium chloride 1.5 g oxyethylenated methyl glucoside dioleate (120 EO) 1 g AM water qs 100 g pH adjusted (NaOH/HCl) 7
• a shampoo in accordance with the invention having the composition below was prepared:
• BEALULIGHT SHAA (Sanyo Kasei) 4.5 g AM AG 10 LK (KAO) 6 g AM STYLEZE CC 10 (ISP) 1 g AM LUVISET PURE (BASF) 4.05 g AM sodium chloride 1.5 g oxyethylenated methyl glucoside dioleate (120 EO) 1.5 g water qs 100 g pH adjusted (NaOH/HCl) 7

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Citations (72)

• 1999
  • 1999-02-03 FR FR9901238A patent/FR2788972B1/fr not_active Expired - Fee Related
• 2000
  • 2000-01-11 DE DE60010538T patent/DE60010538T2/de not_active Expired - Lifetime
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  • 2000-01-11 AT AT00400053T patent/ATE266374T1/de not_active IP Right Cessation
  • 2000-01-27 AU AU13597/00A patent/AU725591B2/en not_active Ceased
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